My little boy is 5 months on Wednesday and for as long as I can remember, he cries when I try to put him down to sleep. So I know he’s chronically over tired because he has such short naps and doesn’t sleep well at night but I’m trying so hard to fix all this. I’ve upgraded to huckleberry plus to test out using wake windows. I tried on the first suggested wake window and he was having none of it, I rock him to sleep and he just didn’t seem tired. I tried 15 mins later and he went down for 20 mins but woke up happy-ish. Just now, he was rubbing his eyes even before I had to give him his bottle (a whole hour before huckleberry’s nap suggestion) I gave him his bottle, then tried to rock him soon after, again crying. I sit down with him, he cries, I rock him, he cries, I put him down with his toys, he cries. In the end I stuck out with bouncing him in the bedroom (our usual routine) and he went off to sleep but where am I going wrong, I follow wake windows and it doesn’t work, I follow his cues, he gets overtired, he has short naps and is just grumpy as a result. When we had a 4 hr car drive a couple of months ago, that was the first and only time he slept well in the day.
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my little boy was also a cryer to fall asleep and I found it so hard! but he seems to have grown out of it - I hope that the same happens for you! I do still use much shorter wake windows than everyone suggests though because I think he has much higher sleep needs than other babies!

also have you tried extending his naps? when my boy was doing short naps I would try and catch it and help him transition back to sleep and he then started extending the naps on his own after a while

Keep trying with Huckleberry because I found it was a lifesaver when my eldest was the same, but it sounds like you need to break the overtired cycle first.
I know it’s shit and drives you mad and will push you to your absolute limits, but when you crack this he will hopefully sleep well day and night 🤞🏼
For now, I would just embrace where he does sleep well. So if he sleeps well in the pram, carrier or contact napping, for the sake of the next few days, use that. Use the 10 min Sweet Spot warning so he’s settled in his sleeping position for when it hits. Most of the time any obvious sleep cues are too late and babe is already overtired, so don’t follow him. Feeding to sleep could also help?
If you have a couple of good sleep days, you’ll be in a much better position to try to get better naps in the cot. (We used sleeping bag, white noise, blind down)
Sleep breeds sleep 🙏🏼🙏🏼🙏🏼 and it does get better, I promise 💓
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